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Volume 68 
Part 12 
Page o3501  
December 2012  

Received 11 November 2012
Accepted 27 November 2012
Online 30 November 2012

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.003 Å
R = 0.046
wR = 0.095
Data-to-parameter ratio = 12.7
Details
Open access

Glabridin

aDepartment of Pharmaceutical Chemistry, Faculty of Pharmaceutical Sciences, Prince of Songkla University and Nanotec-PSU Center of Excellence for Drug Delivery Systems, Hat-Yai, Songkhla 90112, Thailand, and bDepartment of Chemistry and Center of Excellence for Innovation in Chemistry, Faculty of Science, Prince of Songkla University, Hat Yai, Songkhla 90112, Thailand
Correspondence e-mail: vimon.t@psu.ac.th

In the title compound, C20H20O4 {systematic name: 4-[(3R)-8,8-dimethyl-3,4-dihydro-2H-pyrano[2,3-f]chromen-3-yl]benzene-1,3-diol}, the hydropyran ring linked to the pendant benzene ring adopts an envelope conformation, with the methyne C atom forming the flap. In the crystal, the -OH group at the 3-position of the benzene ring forms an O-H...O hydrogen bond to a chromene O-atom acceptor, whereas the -OH group at the 1-position forms an O-H...[pi] interaction with a neighboring benzene ring. The O-H...O hydrogen bonds form [001] chains and the O-H...[pi] bonds cross-link the chains into (101) sheets. The absolute structure was assumed to be the same as that deduced from previous studies for the natural product.

Related literature

For background to the pharmacological activity of the title compound, see: Fukai et al. (2000[Fukai, T., Sakagami, H., Toguchi, M., Takayama, F., Iwakura, I., Atsumi, T., Ueha, T., Nakashima, H. & Nomura, T. (2000). Anticancer Res. 20, 2525-2536.]); Messier & Grenier; (2011[Messier, C. & Grenier, D. (2011). Mycoses, 54, 801-806.]); Thiyagarajan et al. (2011[Thiyagarajan, P., Chandrasekaran, C. V., Deepak, H. B. & Agarwal, A. (2011). Inflammopharmacology, 19, 235-241.]); Ahn et al. (2012[Ahn, J., Lee, H., Jang, J., Kim, S. & Ha, T. (2012). Food Chem Toxicol. 51, 439-445.]); Choi (2005[Choi, E. M. (2005). Biochem. Pharmacol. 70, 363-368.]). For the assignment of the absolute structure, see: Kim et al. (2009[Kim, M., Kim, S.-N., Kim, Y.-U. & Han, J. (2009). Bull. Kor. Chem. Soc. 30, 415-418.]).

[Scheme 1]

Experimental

Crystal data
  • C20H20O4

  • Mr = 324.36

  • Orthorhombic, P 21 21 21

  • a = 6.4301 (4) Å

  • b = 12.0307 (7) Å

  • c = 21.0690 (13) Å

  • V = 1629.87 (17) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.09 mm-1

  • T = 293 K

  • 0.22 × 0.14 × 0.07 mm

Data collection
  • Bruker APEX CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2003[Bruker (2003). SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.984, Tmax = 0.994

  • 15459 measured reflections

  • 2866 independent reflections

  • 2551 reflections with I > 2[sigma](I)

  • Rint = 0.045

Refinement
  • R[F2 > 2[sigma](F2)] = 0.046

  • wR(F2) = 0.095

  • S = 1.16

  • 2866 reflections

  • 225 parameters

  • 2 restraints

  • H atoms treated by a mixture of independent and constrained refinement

  • [Delta][rho]max = 0.15 e Å-3

  • [Delta][rho]min = -0.17 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg4 is the centroid of the C13-C18 ring.

D-H...A D-H H...A D...A D-H...A
O4-H4A...O1i 0.82 (2) 2.02 (2) 2.841 (3) 177 (3)
O3-H3A...Cg4ii 0.80 (2) 2.51 (2) 3.213 (2) 148 (3)
Symmetry codes: (i) [-x+{\script{3\over 2}}, -y+2, z-{\script{1\over 2}}]; (ii) [-x, y+{\script{5\over 2}}, -z+{\script{1\over 2}}].

Data collection: SMART (Bruker, 1998[Bruker (1998). SMART. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2003[Bruker (2003). SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: Mercury (Macrae et al., 2008[Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.]); software used to prepare material for publication: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]) and publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB6989 ).


Acknowledgements

Financial support by the Nanotechnology Center (NANOTEC), NSTDA, Ministry of Science and Technology, Thailand, through Center of Excellence Network program is gratefully acknowledged.

References

Ahn, J., Lee, H., Jang, J., Kim, S. & Ha, T. (2012). Food Chem Toxicol. 51, 439-445.
Bruker (1998). SMART. Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker (2003). SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Choi, E. M. (2005). Biochem. Pharmacol. 70, 363-368.  [CrossRef] [PubMed] [ChemPort]
Fukai, T., Sakagami, H., Toguchi, M., Takayama, F., Iwakura, I., Atsumi, T., Ueha, T., Nakashima, H. & Nomura, T. (2000). Anticancer Res. 20, 2525-2536.  [PubMed] [ChemPort]
Kim, M., Kim, S.-N., Kim, Y.-U. & Han, J. (2009). Bull. Kor. Chem. Soc. 30, 415-418.  [ChemPort]
Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.  [ISI] [CrossRef] [ChemPort] [details]
Messier, C. & Grenier, D. (2011). Mycoses, 54, 801-806.  [CrossRef]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Thiyagarajan, P., Chandrasekaran, C. V., Deepak, H. B. & Agarwal, A. (2011). Inflammopharmacology, 19, 235-241.  [CrossRef] [ChemPort] [PubMed]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [ISI] [CrossRef] [ChemPort] [details]


Acta Cryst (2012). E68, o3501  [ doi:10.1107/S1600536812048647 ]

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